EP2806008A1 - Dispositif électroluminescent organique utilisant un composé électroluminescent organique comme matériau électroluminescent - Google Patents

Dispositif électroluminescent organique utilisant un composé électroluminescent organique comme matériau électroluminescent Download PDF

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EP2806008A1
EP2806008A1 EP20140173174 EP14173174A EP2806008A1 EP 2806008 A1 EP2806008 A1 EP 2806008A1 EP 20140173174 EP20140173174 EP 20140173174 EP 14173174 A EP14173174 A EP 14173174A EP 2806008 A1 EP2806008 A1 EP 2806008A1
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Prior art keywords
substituted
unsubstituted
alkyl
aryl
compound
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German (de)
English (en)
Inventor
Chi Sik Kim
Soo Yong Lee
Young Gil Kim
Hyo-Jung Lee
Su Hyun Lee
Hyun Kim
Young Jun Cho
Hoon Chang
Kyung Joo Lee
Bong-Ok Kim
Sung-Min Kim
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Rohm and Haas Electronic Materials Korea Ltd
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Rohm and Haas Electronic Materials Korea Ltd
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Publication of EP2806008A1 publication Critical patent/EP2806008A1/fr
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Definitions

  • the present invention relates to an organic electroluminescent device, and more particularly to an organic electroluminescent device where an organic layer is interposed between an anode and a cathode on a substrate, the organic layer including an electroluminescent layer containing one or more dopant compounds represented by Chemical Formula 1 below and one or more host compounds represented by Chemical Formulas 2 to 5 below.
  • an electroluminescent device is a self-luminescent display device, and has advantages of wider viewing angel as compared with LCD, excellent contrast, and fast response speed.
  • An organic EL device which uses aromatic diamine having a low molecular weight, and an aluminum complex, as a material for forming an electroluminescent layer, was first developed by Eastman Kodak Company in 1987 [ Appl. Phys. Lett. 51, 913, 1987 ].
  • the organic EL device when charges are injected to an organic film formed between an electron injection electrode (cathode) and a hole injection electrode (anode), electrons and holes pair up and become extinct while light is emitted.
  • the organic EL device has advantages in that elements can be formed on a flexible transparent substrate such as plastics, and it can be driven at a low voltage (10V or lower) as compared with a plasma display panel or an inorganic EL display.
  • the organic EL device requires relatively small power consumption and has excellent color. Meanwhile, the organic EL device exhibits three colors, red, green, and blue, and thus it become an object of attention from many people as a next colorful display device.
  • An organic material for the organic EL device may be largely divided into an electroluminescent material and a charge transport material.
  • the electroluminescent material is directly related to electroluminescent color and luminous efficiency, and requires several characteristics such as a high fluorescence quantum yield in a solid state, high mobility of electrons and holes, low degradability at the time of vacuum deposition, and uniform thin-film formability.
  • the electroluminescent material may be divided into a host material and a dopant material in view of function.
  • a device having a structure where an electroluminescent layer is formed by doping a host with dopants has been known to have excellent EL characteristic.
  • Recently, development of organic EL device having high efficiency and long life property is becoming the most urgent issue, and particularly, development of materials more excellent than the existing electroluminescent materials is urgent, considering EL characteristic levels required for medium-large sized OLED panels. For this reason, the host material functioning as a solvent of solid state and an energy transferring member needs to have high purity, and appropriate molecular weight for enabling vacuum deposition.
  • the host material needs to secure high thermal stability due to high glass transition temperature and high thermal decomposition temperature, and high electrochemical stability for long life property. Furthermore, the host material needs to be easy in the formation of amorphous thin film, and have excellent adhesive strength with materials of adjacent other layers while motion between layers need not occur.
  • a fluorescent material has been widely used until now, as the electroluminescent material functioning as the most important factor determining the luminous efficiency of the OLED, but development of a phosphorescent material is known to the best method that can improve the luminous efficiency theoretically up to four times in an electroluminescent mechanism.
  • CBP As a host material of a phosphorescence electroluminescent body, CBP is the most widely known until now, and a high-efficiency OLED to which a hole blocking layer of CBP or BAlq is applied is known.
  • An OLED using an actual phosphorescence electroluminescent material has a higher current efficiency (cd/A) as compared with an OLED using a fluorescence electroluminescent material.
  • an OLED where the existing materials such as BAlq or CBP is used as a host of a phosphorescence electroluminescent material has a higher driving voltage as compared with the OLED using a fluorescent material, and thus, large advantages are not present in view of power efficiency (1m/w).
  • an organic electroluminescent device having high color purity, high brightness, and long life property can be realized by interposing an organic layer, which includes an electroluminescent layer made by a combination of particular compounds, between an anode and a cathode on a substrate.
  • An object of the present invention is to provide an organic electroluminescent device where an organic layer is interposed between an anode and a cathode on a substrate, the organic layer including an electroluminescent layer containing one or more host compounds and one or more dopant compounds, and thus, an organic electroluminescent device having excellent luminous efficiency, high color purity, low driving voltage, and long life property.
  • the present invention is directed to an organic electroluminescent device, and more specifically, an organic electroluminescent device where an organic layer is interposed between an anode and a cathode on a substrate, the organic layer including an electroluminescent layer containing one or more dopant compounds represented by Chemical Formula 1 below and one or more host compounds represented by Chemical Formulas 2 to 5 below.
  • the organic electroluminescent device according to the present invention exhibits a host-dopant energy transfer mechanism, and thus, can express a certain high-efficiency electroluminescent performance, based on improved electron density distribution. Further, the organic electroluminescent device according to the present invention can overcome low initial efficiency, short operation life property, or the like, and secure high-performance electroluminescent performance with high efficiency and long life property for each color.
  • the compound represented by Chemical Formula 1 included as a dopant may include the compounds represented by Chemical Formulas 6 and 7, the compound represented by Chemical Formula 2 included as a host may include the compounds represented by Chemical Formulas 8 to 13, and Cz of the Chemical Formulas 3 to 4 above may include the following structures, but are not limited thereto. [wherein
  • L 1 represented by Chemical Formula 1 may be selected from following structures, but is not limited thereto. [wherein
  • substitutions including “alkyl” “alkoxy”, and, besides, “alkyl” moieties may include both linear and branched species, and "cycloalkyl” may include monocyclic hydrocarbon as well as polycyclic hydrocarbon such as substituted or unsubstituted adamantyl or substituted or unsubstituted (C7-C30)bicycloalkyl.
  • aryl means an organic radical derived from aromatic hydrocarbon by the removal of one hydrogen atom, and may include a single ring or a fused ring containing properly 4 to 7 ring atoms, preferably 5 or 6 ring atoms, and even may include a structure where a plurality of aryls are linked by single bonds. Specific examples thereof include phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, triphenylenyl, pyrenyl, perylenyl, chrysenyl, naphthacenyl, fluoranthenyl, or the like, but are not limited thereto.
  • the naphthyl includes 1-naphthyl and 2-naphthyl
  • the anthryl includes 1-anthryl, 2-anthryl and 9-anthryl
  • the phenanthryl includes 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, and 9-phenanthryl
  • the naphthacenyl includes 1-naphthacenyl, 2-naphthacenyl, and 9-naphthacenyl.
  • the pyrenyl includes 1-pyrenyl, 2-pyrenyl, and 4-pyrenyl
  • the biphenyl includes 2-biphenyl, 3-biphenyl, and 4-biphenyl.
  • the terphenyl includes p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, and m-terphenyl-2-yl group.
  • the fluorenyl includes 1-fluorenyl, 2-fluorenyl, 3-fluorenyl, 4-fluorenyl and 9-fluorenyl.
  • heteroaryl include a form where one or more heteroaryls are liked by single bonds.
  • the heteroaryl group includes a divalent aryl group wherein the heteroatom(s) in the ring may be oxidized or quaternized to form, for example, N- oxide or quaternary salt.
  • Specific examples include monocyclic heteroaryl such as furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, or the like, polycyclic heteroaryl such as benzofuranyl, benzothiophenyl, dibenzofuranyl, dibenzothiopenyl, isobenzofuranyl, benzimidazolyl
  • the pyrrolyl includes 1-pyrrolyl, 2-pyrrolyl, and 3-pyrrolyl; the pyridyl includes 2-pyridyl, 3-pyridyl, and 4-pyridyl; the indolyl includes 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, and 7-indolyl; the isoindolyl includes 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, and 7-isoindolyl; the furyl includes 2-furyl, and 3-furyl; the benzofuranyl includes 2-benzofuranyl, 3-benzofuranyl, 4-benzofuranyl, 5-benzofuranyl, 6-benzofuranyl, and 7-benzofuranyl;
  • (C3-C30)heteroaryl may include (C3-C20)heteroaryl or (C3-C12)heteroaryl
  • (C3-C30)cycloalkyl may include (C3-C20)cycloalkyl or (C3-C7)cycloalkyl
  • (C2-C30)alkenyl or alkynyl may include (C2-C20)alkenyl or alkynyl, or (C2-C10)alkenyl or alkynyl.
  • substituted in “substituted or unsubstituted”, means to be further substituted with an unsubstituted substituent.
  • substituents further substituted with the R, R 1 through R 9 , R 1 through R 12 , R 31 through R 32 , R 41 through R 45 , R 51 through R 53 , R 61 through R 69 , R 71 through R 84 , L 2 , M and Ar 1 independently represent one or more selected from the group consisting of deuterium, halogen, halogen-substituted or unsubstituted (C1-C30)alkyl, (C6-C30)aryl, (C6-C30)aryl-substituted or unsubstituted (C3-C30)heteroaryl, 5- to 7-membered heterocycloalkyl, 5- to 7-membered heterocycloalkyl fused with one or more aromatic rings, (C3-C30)
  • organic electroluminescent compounds of Chemical Formulas 2 to 5 may be exemplified by the following compounds, which are not intended to limit the present invention.
  • the compound of Chemical Formula 1 may be prepared as shown in Scheme 1.
  • the following preparing method is not intended to limit a method for preparing the organic electroluminescent compound of Chemical Formula 1, and modifications of the following preparing method would be obvious to those skilled in the art.
  • the electroluminescent layer means a layer where electroluminescence occurs. It may have a single layer or a plurality of layers where two or more layers are stacked. In case a combination of a dopant and a host is used in the present invention, remarkable improvement in luminous efficiency may be confirmed.
  • a doping concentration of the dopant compound based on the host compound in the electroluminescent layer is in a range of below 20 wt%.
  • the organic layer may further contain one or more metals selected from the group consisting of organic metals of Group 1, Group 2, 4 th period and 5 th period transition metals, lanthanide metals, and d-transition elements in the Periodic Table of Elements or complex compounds, besides the organic electroluminescent compounds of Chemical Formulas 1 to 4.
  • the organic layer may include both an electroluminescent layer and a charge generating layer.
  • the organic layer may include the organic electroluminescent compounds of Chemical Formulas 1 to 4, and at the same time include one or more compounds selected from the group consisting of arylamine-based compounds and styrylarylamine-based compounds.
  • arylamine-based compounds or the styrylarylamine-based compounds are described on paragraphs ⁇ 212> to ⁇ 224> in the specification of Korean Patent Application No. 10-2008-0060393 , but are not limited thereto.
  • Specific examples of the organic electroluminescent compounds of Chemical Formulas 2 to 4 are exemplified in Korean Patent Application Nos.
  • the organic layer may further include one or more organic electroluminescent layers containing red, green, or blue electroluminescent compounds besides the organic electroluminescent compound at the same time, thereby manufacturing an organic electroluminescent device for emitting white light.
  • the compounds for emitting red, green, or blue light are exemplified in Korean Patent Application Nos. 10-2008-0123276 , 10-2008-0107606 , or 10-2008-0118428 , but are not limited thereto.
  • the organic electroluminescent device of the present invention it is preferable to arrange at least one layer (hereinafter, referred to as "surface layer") selected from chalcogenide layers, metal halide layers, and metal oxide layers, on the inside surface of at least one side of a pair of electrodes. Specifically, it is preferable to arrange a chalcogenide (including oxides) layer of silicon and aluminum metal on an anode surface of an electroluminescent medium layer, and a metal halide layer or a metal oxide layer on a cathode surface of the electroluminescent medium layer. This enables driving stability to be obtained.
  • Examples of the chalcogenides may include SiO x (1 ⁇ X ⁇ 2), AlO X (1 ⁇ X ⁇ 1.5), SiON, SiAlON, and the like
  • examples of the metal halides may include LiF, MgF 2 , CaF 2 , rare earth metal fluoride, and the like
  • examples of the metal oxides may include Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.
  • the organic electroluminescent device of the present invention it is also preferable to arrange a mixed region of an electron transport compound and a reductive dopant or a mixed region of a hole transport compound and an oxidative dopant on a surface of at least one of the pair of electrodes thus manufactured. Therefore, the electron transport compound is reduced into an anion, which facilitates to inject or transport electrons into the electroluminescent medium from the mixed region.
  • the hole transport compound is oxidized into a cation, which facilitates to inject or transport holes into the electroluminescent medium from the mixed region.
  • Preferable oxidative dopants include various Lewis acids and acceptor compounds.
  • Preferable reductive dopants include alkaline metals, alkaline metal compounds, alkaline earth metals, rare-earth metals, and mixtures thereof.
  • a layer of the reductive dopant may be used as the charge generating layer to manufacture a white organic electroluminescent device having two or more electroluminescent layers.
  • an organic electroluminescent device using a specific dopant-host organic electroluminescent compound according to the present invention had better luminous efficiency and longer operation life at a lower driving voltage as compared with a device using the existing electroluminescent material. It is considered that a specific combination of dopant and host has a comparative proper level of energy to show excellent luminous efficiency and long operation life.
  • Compound 6-1 28g (100.68mmol) was mixed with triethylphosphite 300ml, and then the mixture was stirred at 150 . After 6 hours, the resultant material was cooled to room temperature, and then distilled under reduced pressure, followed by extraction with EA and wash with distilled water. Then, drying over magnesium sulfate, distillation under reduced pressure, and then column separation were performed, thereby obtaining Compound 6-2 11g(44.69mmol, 44.38%).
  • 1,3-Dibromobenzene 20 g (84.77 mmol) was dissolved in THF 500 mL, and then cooled to a temperature of -78 n-BuLi 2.5M 33.9 mL(84.77 mmol) was slowly added thereinto, and then stirred at a temperature of -78 for 1 hour.
  • Chlorotriphenylsilane ((C 6 H 5 ) 3 SiCl) 29.9 g was dissolved in THF 100 mL, and this solution was added into the above reaction mixture. The resultant mixture was slowly warmed to room temperature, and stirred for 12 hours.
  • 1,3-Dibromobenzene 28 g(0.119 mol) was dissolved in THF 600 mL, and then n-BuLi 47.5 mL was slowly added dropwise thereto at -78°C, followed by stirring for 1 hour.
  • 2-Chloro-4,6-diphenyl-1,3,5-triazine 47.5 mL was slowly added dropwise thereto, and the resultant mixture was stirred at room temperature for 5 hours after the temperature was slowly raised. After the reaction is completed, extraction with EA and distilled water and column separation were sequentially performed, thereby obtaining Compound 9-1 15.7 g (40.43 mmol, 40.4%).
  • Dibenzo[b,d]furan-4-ylboronic acid 10 g (43.84mmol), bromonitrobenzene 8.85g (43.84mmol), 2M aqueous Na 2 CO 3 solution 70ml, toluene 200ml, and ethanol 70ml were mixed, and then stirred under reflux. After 5 hours, the resultant material was cooled to room temperature, and then extracted with EA, followed by wash with distilled water. Then, drying over magnesium sulfate, distillation under reduced pressure, and column separation were sequentially performed, thereby obtaining Compound 11-1 10g (32.74mmol, 74.68%).
  • Dibenzo[b,d]thiophen-4-ylboronic acid 10 g (43.84mmol), bromonitrobenzene 8.85g (43.84mmol), 2M aqueous Na 2 CO 3 solution 70ml, toluene 200ml, and ethanol 70ml were mixed, and then stirred under reflux. After 5 hours, the resultant material was cooled to room temperature, and then extracted with EA, followed by wash with distilled water. Then, drying over magnesium sulfate, distillation under reduced pressure, and column separation were sequentially performed, thereby obtaining Compound 12-1 10g (32.74mmol, 74.68%).
  • Carbazole (30g, 0.18mol), 1,4-dibromobenzene (85g, 0.36mol), CuI (34g, 0.18mol), K 3 PO 4 (114g, 0.54mol), and toluene(1200ml) were put into a 500mL round-bottom flask, and the resultant mixture was stirred at 120 for 10 minutes. Then, ethylenediamine (24ml, 0.36mol) was added thereinto, followed by stirring at 120 for 12 hours. After completion of the reaction, extraction with ethyl acetate was performed on the resultant material, followed by column chromatography, thereby obtaining a compound.
  • 2,8-dibromodibenzo[b,d]thiophene 20g (0.12 mol), carbazole 82g (2eq), CuI 11.4g (0.5eq) and K 3 PO 4 76.1g (3eq) were put into a 2-neck flask, which is then filled with nitrogen under vacuum ambient Then, toluene mL(0.1M) was added thereinto, followed by stirring under reflux at 80. When the temperature reached 80 , ethylenediamine 8mL (1eq) was added thereinto, followed by stirring under reflux at 120 for 12 hours. After completion of the reaction, NH 4 Cl(aq) 100mL was added thereinto and Cu was removed.
  • An OLED device was manufactured by using the electroluminescent material of the present invention.
  • a transparent electrode ITO thin film (15 ⁇ / ⁇ ) obtained from a glass for OLED (manufactured by Samsung Corning) was subjected to ultrasonic washing with trichloroethylene, acetone, ethanol and distilled water, sequentially, and stored in isopropanol before use.
  • the ITO substrate was mounted on a substrate holder of a vacuum deposition apparatus, and N1,N1'-(biphenyl-4,4'-diyl)bis(N1-(naphthalen-2-yl)-N4,N4-diphenylbenzene-1,4-diamine) was put in a cell of the vacuum deposition apparatus, which was then evacuated until vacuum degree in the chamber reached to 10 -6 torr. Then, electric current was applied to the cell to perform vaporization, thereby forming a hole injection layer having a thickness of 120 nm on the ITO substrate.
  • N4,N4,N4',N4'-tetra(biphenyl-4-yl)biphenyl-4,4'-diamine was put in another cell of the vacuum vapor deposition apparatus, and electric current was applied to the cell to perform vaporization, thereby forming a hole transport layer having a thickness of 20 nm on the hole injection layer.
  • an electroluminescent layer was formed thereon as follows. Compound 53 as a host was put in a cell and Compound 1 as a dopant was put in another cell, within a vacuum vapor deposition apparatus.
  • the two materials were vaporized at different rates to perform doping of below 20 wt%, thereby forming an electroluminescent layer having a thickness of 40 nm on the hole transport layer.
  • 2-(4-(9,10-di(naphthalen-2-yl)anthracen-2-yl)phenyl)-1-phenyl-1H-benzo[d]imidazole) was put in put in a cell of the vacuum deposition apparatus, and Lithium quinolate was put in another cell of the vacuum deposition apparatus.
  • the two materials were vaporized at different rates to perform doping of 30 wt% to 70 wt%, thereby forming an electron transfer layer having a thickness of 30 nm on the electroluminescent layer.
  • lithium quinolate was deposited to have a thickness of 1 to 2 nm as an electron injection layer, and then an A1 cathode is deposited to have a thickness of 150nm by using another vacuum deposition apparatus, thereby manufacturing an OLED device.
  • Respective compounds according to the materials were purified by vacuum sublimation under 10-6 torr.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 54 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 59 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 62 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 63 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compounds 63 and 48 were evaporated at the same speed and used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 65 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 66 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 71 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 77 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compounds 78 and 48 were evaporated at the same speed and used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 94 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 95 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 96 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, as electroluminescent materials, Compound 97 was used as a host.
  • An OLED device was manufactured by the same method as Example 1 except that, an electroluminescent layer having a thickness of 30 nm is deposited on a hole transfer layer by using CBP[4,4'-N,N'-dicarbazole-biphenyl] as a host and Ir(ppy)3[tris(2-phenylpyridine)iridium as a dopant, as electroluminescent materials, and a hole blocking layer having a thickness of 10 nm is deposited by using BAlq[bis(2-methyl-8-quinolinate)(p-phenylphenolato) aluminum (III).
  • An OLED device was manufactured by the same method as Example 1 except that, an electroluminescent layer having a thickness of 30 nm is deposited on a hole transfer layer by using Compound 66 as a host and Ir(ppy)3 [tris(2-phenylpyridine)iridium] as a dopant, as electroluminescent materials.
  • An OLED device was manufactured by the same method as Example 1 except that, an electroluminescent layer having a thickness of 30 nm is deposited on a hole transfer layer by using Compound 66 as a host and Compound 30 as a dopant, as electroluminescent materials.
  • test data confirmed that when the specific host according to an exemplary embodiment and tris(4-methyl-2,5-diphenylpyridine)Iridium were used together on the electroluminescent layer, excellent luminescent efficiency and long operation life were exhibited.
  • the dopant according to an exemplary embodiment showed excellent properties when the dopant was used with two hosts.

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KR20140058454A (ko) 2014-05-14
CN103140564A (zh) 2013-06-05
KR20120012431A (ko) 2012-02-09
JP2019195074A (ja) 2019-11-07
WO2012015274A2 (fr) 2012-02-02
KR20140051871A (ko) 2014-05-02
JP2016189468A (ja) 2016-11-04
EP2599851A4 (fr) 2013-12-11
US20140054564A1 (en) 2014-02-27
EP2857395A1 (fr) 2015-04-08
WO2012015274A3 (fr) 2012-03-22
JP2013539206A (ja) 2013-10-17
KR20140051872A (ko) 2014-05-02
EP2905281A1 (fr) 2015-08-12
CN103140564B (zh) 2015-11-25
EP2599851A2 (fr) 2013-06-05

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